NPASS Compound

Structure

CID317383 OpenBabel06191716142D 37 38 0 0 1 0 0 0 0 0999 V2000 6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 12 14 2 0 0 0 0 13 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 19 3 1 1 0 0 0 19 29 1 0 0 0 0 20 23 2 0 0 0 0 20 27 1 0 0 0 0 21 5 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 14 1 1 0 0 0 22 33 1 0 0 0 0 23 37 1 0 0 0 0 24 26 1 0 0 0 0 24 34 1 0 0 0 0 25 28 2 0 0 0 0 25 35 1 0 0 0 0 26 27 1 0 0 0 0 26 30 2 0 0 0 0 27 31 2 0 0 0 0 28 30 1 0 0 0 0 28 32 1 0 0 0 0 29 36 1 6 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.29
Volume:	550.763
LogP:	4.323
LogD:	3.418
LogS:	-4.506
# Rotatable Bonds:	13
TPSA:	87.36
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	4.632
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.612
MDCK Permeability:	1.1881024875037838e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.306
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	94.07967376708984%
Volume Distribution (VD):	0.712
Pgp-substrate:	12.570813179016113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.375
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.848
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.559
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.774
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	5.368
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.841
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.352
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.639
Carcinogencity:	0.117
Eye Corrosion:	0.006
Eye Irritation:	0.031
Respiratory Toxicity:	0.841

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC317383

Natural Product ID:	NPC317383
*Common Name:**	Stigmatellin
IUPAC Name:	2-[(3S,4S,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trienyl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one
Synonyms:	Stigmatellin
Standard InCHIKey:	UZHDGDDPOPDJGM-CVOZLMQJSA-N
Standard InCHI:	InChI=1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1
SMILES:	CC=C(C)C=CC=CC(C(C)C(C(C)CCC1=C(C(=O)C2=C(O1)C(=C(C=C2OC)OC)O)C)OC)OC
Synthetic Gene Cluster:	BGC0000153;
ChEMBL Identifier:	CHEMBL486556
PubChem CID:	447884
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18701458]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18989924]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21979787]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22741921]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22907798]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24367422]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3106289]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	5

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	>	180.0	uM	PMID[486660]
NPT2	Others	Unspecified	IC50	=	81.0	nM	PMID[486660]
NPT2	Others	Unspecified	Activity	=	180.0	uM	PMID[486660]
NPT2	Others	Unspecified	IC50	=	9.1	nM	PMID[486661]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC317383 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	1553
0.2-0.3	4265
0.3-0.4	10019
0.4-0.5	8147
0.5-0.6	3801
0.6-0.7	5087
0.7-0.8	5383
0.8-0.85	2339
0.85-0.9	1230
0.9-0.95	451
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC222814
0.9539	High Similarity	NPC96167
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC472913
0.9539	High Similarity	NPC245758
0.9539	High Similarity	NPC470402
0.9539	High Similarity	NPC472914
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC472910
0.9539	High Similarity	NPC472911
0.9536	High Similarity	NPC213622
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC255106
0.947	High Similarity	NPC183878
0.947	High Similarity	NPC47781
0.947	High Similarity	NPC160951
0.947	High Similarity	NPC22519
0.947	High Similarity	NPC176775
0.947	High Similarity	NPC231018
0.947	High Similarity	NPC255350
0.947	High Similarity	NPC145379
0.947	High Similarity	NPC69394
0.947	High Similarity	NPC274327
0.9459	High Similarity	NPC61871
0.9459	High Similarity	NPC55557
0.9459	High Similarity	NPC30647
0.9412	High Similarity	NPC469584
0.9412	High Similarity	NPC99597
0.9412	High Similarity	NPC210084
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC4455
0.9408	High Similarity	NPC146165
0.9408	High Similarity	NPC256612
0.9408	High Similarity	NPC128863
0.9408	High Similarity	NPC92659
0.9408	High Similarity	NPC20830
0.9408	High Similarity	NPC183597
0.9408	High Similarity	NPC227325
0.9408	High Similarity	NPC2476
0.9408	High Similarity	NPC138360
0.9408	High Similarity	NPC280339
0.9408	High Similarity	NPC196439
0.9408	High Similarity	NPC163780
0.9408	High Similarity	NPC167815
0.9408	High Similarity	NPC50715
0.9408	High Similarity	NPC472909
0.9408	High Similarity	NPC201136
0.9404	High Similarity	NPC71334
0.9404	High Similarity	NPC256283
0.9404	High Similarity	NPC100887
0.9404	High Similarity	NPC188203
0.9404	High Similarity	NPC241498
0.9404	High Similarity	NPC120163
0.9404	High Similarity	NPC83508
0.9404	High Similarity	NPC293183
0.9404	High Similarity	NPC301323
0.9404	High Similarity	NPC275836
0.9404	High Similarity	NPC275722
0.9404	High Similarity	NPC212678
0.9404	High Similarity	NPC162313
0.9404	High Similarity	NPC198826
0.9404	High Similarity	NPC187498
0.9404	High Similarity	NPC25270
0.9404	High Similarity	NPC156222
0.9404	High Similarity	NPC239128
0.9404	High Similarity	NPC131624
0.9404	High Similarity	NPC222830
0.9404	High Similarity	NPC57030
0.9355	High Similarity	NPC266314
0.9351	High Similarity	NPC250214
0.9351	High Similarity	NPC95936
0.9346	High Similarity	NPC472916
0.9346	High Similarity	NPC49824
0.9342	High Similarity	NPC276409
0.9342	High Similarity	NPC75279
0.9342	High Similarity	NPC18727
0.9342	High Similarity	NPC124714
0.9342	High Similarity	NPC280937
0.9342	High Similarity	NPC250822
0.9338	High Similarity	NPC208043
0.9338	High Similarity	NPC226973
0.9304	High Similarity	NPC470456
0.9295	High Similarity	NPC81679
0.929	High Similarity	NPC476980
0.929	High Similarity	NPC263449
0.9286	High Similarity	NPC129684
0.9286	High Similarity	NPC101830
0.9286	High Similarity	NPC181960
0.9286	High Similarity	NPC224137
0.9286	High Similarity	NPC93376
0.9286	High Similarity	NPC75215
0.9286	High Similarity	NPC189179
0.9286	High Similarity	NPC223787
0.9286	High Similarity	NPC299520
0.9286	High Similarity	NPC110070
0.9286	High Similarity	NPC227192
0.9286	High Similarity	NPC203891
0.9286	High Similarity	NPC78225
0.9281	High Similarity	NPC201451
0.9281	High Similarity	NPC208197
0.9281	High Similarity	NPC2928
0.9281	High Similarity	NPC26227
0.9281	High Similarity	NPC44079
0.9276	High Similarity	NPC245382
0.9276	High Similarity	NPC121522
0.9276	High Similarity	NPC236637
0.9276	High Similarity	NPC131266
0.9276	High Similarity	NPC269451
0.9276	High Similarity	NPC291802
0.9276	High Similarity	NPC120537
0.9276	High Similarity	NPC100971
0.9276	High Similarity	NPC180234
0.9276	High Similarity	NPC39732
0.9276	High Similarity	NPC472912
0.9276	High Similarity	NPC181209
0.9276	High Similarity	NPC302950
0.9276	High Similarity	NPC100263
0.9276	High Similarity	NPC35763
0.9276	High Similarity	NPC209487
0.9276	High Similarity	NPC216769
0.9276	High Similarity	NPC219582
0.9276	High Similarity	NPC142540
0.9276	High Similarity	NPC60972
0.9276	High Similarity	NPC199100
0.9272	High Similarity	NPC184136
0.9272	High Similarity	NPC306821
0.9262	High Similarity	NPC226987
0.9262	High Similarity	NPC143903
0.9241	High Similarity	NPC470462
0.9231	High Similarity	NPC258331
0.9231	High Similarity	NPC308992
0.9226	High Similarity	NPC469658
0.9226	High Similarity	NPC22472
0.9226	High Similarity	NPC191459
0.9226	High Similarity	NPC288669
0.9226	High Similarity	NPC204854
0.9226	High Similarity	NPC130894
0.9226	High Similarity	NPC7846
0.9226	High Similarity	NPC18772
0.9226	High Similarity	NPC300943
0.9226	High Similarity	NPC152166
0.9226	High Similarity	NPC105242
0.9226	High Similarity	NPC9609
0.9226	High Similarity	NPC115798
0.9226	High Similarity	NPC25495
0.9226	High Similarity	NPC4481
0.9226	High Similarity	NPC19687
0.9226	High Similarity	NPC143828
0.9226	High Similarity	NPC253634
0.9226	High Similarity	NPC176300
0.9226	High Similarity	NPC18607
0.9226	High Similarity	NPC261004
0.9226	High Similarity	NPC152904
0.9221	High Similarity	NPC291878
0.9221	High Similarity	NPC472626
0.9221	High Similarity	NPC195796
0.9221	High Similarity	NPC292107
0.9221	High Similarity	NPC470328
0.9221	High Similarity	NPC474520
0.9221	High Similarity	NPC209614
0.9221	High Similarity	NPC245546
0.9221	High Similarity	NPC98661
0.9221	High Similarity	NPC43243
0.9221	High Similarity	NPC278778
0.9221	High Similarity	NPC68093
0.9221	High Similarity	NPC247017
0.9221	High Similarity	NPC191146
0.9221	High Similarity	NPC35038
0.9221	High Similarity	NPC266960
0.9216	High Similarity	NPC472915
0.9216	High Similarity	NPC250557
0.9216	High Similarity	NPC86485
0.9216	High Similarity	NPC88645
0.9216	High Similarity	NPC292214
0.9216	High Similarity	NPC271779
0.9216	High Similarity	NPC206238
0.9216	High Similarity	NPC167091
0.9211	High Similarity	NPC117579
0.9211	High Similarity	NPC19980
0.9211	High Similarity	NPC308451
0.9211	High Similarity	NPC45291
0.9211	High Similarity	NPC262623
0.9211	High Similarity	NPC475076
0.9211	High Similarity	NPC204515
0.9205	High Similarity	NPC223579
0.9205	High Similarity	NPC328119
0.9205	High Similarity	NPC287101
0.9205	High Similarity	NPC48479
0.9205	High Similarity	NPC92722
0.9205	High Similarity	NPC17286
0.9205	High Similarity	NPC183950
0.9205	High Similarity	NPC102003
0.9205	High Similarity	NPC177298
0.9205	High Similarity	NPC259713
0.9205	High Similarity	NPC216318
0.9205	High Similarity	NPC137062

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC317383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	912
0.2-0.3	1955
0.3-0.4	2629
0.4-0.5	1768
0.5-0.6	946
0.6-0.7	406
0.7-0.8	114
0.8-0.85	31
0.85-0.9	13
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD2801	Approved
0.9276	High Similarity	NPD1934	Approved
0.9091	High Similarity	NPD2393	Clinical (unspecified phase)
0.8974	High Similarity	NPD3882	Suspended
0.8874	High Similarity	NPD1511	Approved
0.8827	High Similarity	NPD3818	Discontinued
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.8773	High Similarity	NPD7054	Approved
0.8758	High Similarity	NPD1512	Approved
0.872	High Similarity	NPD7472	Approved
0.872	High Similarity	NPD7074	Phase 3
0.8688	High Similarity	NPD5494	Approved
0.8675	High Similarity	NPD4338	Clinical (unspecified phase)
0.8671	High Similarity	NPD3817	Phase 2
0.8503	High Similarity	NPD7251	Discontinued
0.85	High Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7808	Phase 3
0.8443	Intermediate Similarity	NPD6797	Phase 2
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8293	Intermediate Similarity	NPD1247	Approved
0.8289	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1510	Phase 2
0.821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD5402	Approved
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD6232	Discontinued
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6801	Discontinued
0.8079	Intermediate Similarity	NPD943	Approved
0.8079	Intermediate Similarity	NPD1240	Approved
0.8037	Intermediate Similarity	NPD7819	Suspended
0.8026	Intermediate Similarity	NPD230	Phase 1
0.8012	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1607	Approved
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7952	Intermediate Similarity	NPD919	Approved
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7908	Intermediate Similarity	NPD447	Suspended
0.7898	Intermediate Similarity	NPD2800	Approved
0.7881	Intermediate Similarity	NPD3027	Phase 3
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.787	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD6959	Discontinued
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.784	Intermediate Similarity	NPD1653	Approved
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7805	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD5403	Approved
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7756	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD9494	Approved
0.7742	Intermediate Similarity	NPD6651	Approved
0.7736	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD920	Approved
0.7654	Intermediate Similarity	NPD5401	Approved
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7632	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7625	Intermediate Similarity	NPD3750	Approved
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7595	Intermediate Similarity	NPD6100	Approved
0.7595	Intermediate Similarity	NPD6099	Approved
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5353	Approved
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3749	Approved
0.7469	Intermediate Similarity	NPD6190	Approved
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1243	Approved
0.744	Intermediate Similarity	NPD37	Approved
0.7438	Intermediate Similarity	NPD2344	Approved
0.7429	Intermediate Similarity	NPD7228	Approved
0.7429	Intermediate Similarity	NPD3751	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4966	Approved
0.7412	Intermediate Similarity	NPD4965	Approved
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD6844	Discontinued
0.7314	Intermediate Similarity	NPD2403	Approved
0.7312	Intermediate Similarity	NPD3748	Approved
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7278	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD8312	Approved
0.7262	Intermediate Similarity	NPD3226	Approved
0.7261	Intermediate Similarity	NPD2313	Discontinued
0.7257	Intermediate Similarity	NPD5242	Approved
0.7256	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7233	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4363	Phase 3
0.7204	Intermediate Similarity	NPD4360	Phase 2
0.719	Intermediate Similarity	NPD9717	Approved
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7178	Intermediate Similarity	NPD2424	Discontinued
0.7176	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD6385	Approved
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1203	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7134	Intermediate Similarity	NPD2654	Approved
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2346	Discontinued
0.7115	Intermediate Similarity	NPD2798	Approved
0.7107	Intermediate Similarity	NPD6233	Phase 2
0.7105	Intermediate Similarity	NPD6782	Approved
0.7105	Intermediate Similarity	NPD6780	Approved
0.7105	Intermediate Similarity	NPD6776	Approved
0.7105	Intermediate Similarity	NPD6781	Approved
0.7105	Intermediate Similarity	NPD6777	Approved
0.7105	Intermediate Similarity	NPD6779	Approved
0.7105	Intermediate Similarity	NPD6778	Approved
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.7091	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4110	Phase 3
0.7086	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD7435	Discontinued
0.7078	Intermediate Similarity	NPD1608	Approved
0.7066	Intermediate Similarity	NPD7390	Discontinued
0.7062	Intermediate Similarity	NPD7584	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7044	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6798	Discontinued
0.7044	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD9268	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.7032	Intermediate Similarity	NPD4749	Approved
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.7	Intermediate Similarity	NPD6671	Approved
0.6995	Remote Similarity	NPD7697	Approved
0.6995	Remote Similarity	NPD7696	Phase 3
0.6995	Remote Similarity	NPD7698	Approved
0.6994	Remote Similarity	NPD5761	Phase 2
0.6994	Remote Similarity	NPD5760	Phase 2
0.699	Remote Similarity	NPD8151	Discontinued
0.6984	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4361	Phase 2
0.6978	Remote Similarity	NPD7240	Approved
0.6978	Remote Similarity	NPD6104	Discontinued
0.6974	Remote Similarity	NPD9545	Approved
0.6964	Remote Similarity	NPD4357	Discontinued
0.6962	Remote Similarity	NPD3018	Phase 2
0.6959	Remote Similarity	NPD7871	Phase 2
0.6959	Remote Similarity	NPD7458	Discontinued
0.6959	Remote Similarity	NPD7870	Phase 2
0.6959	Remote Similarity	NPD228	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data